The Bet
by RocketJones
Summary: Oliver.Rico. Bet. Miley. Virginity. Dance. Hotdog.Suck. Bad Words. Teen sex talk. Warning.That's all. Loliver
1. Chapter 1

**Chapter 1**

Disclaimer- I don't own Hannah Montana. At all…

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"Oliver,"

"OLIVER"

"OOOO LLLL IIII VVV EEE RRR"

"What?!" shouted Oliver as he woke up from his sleep. Drool had become almost like a river on the valley that was his desk. Ahh crap he thought as he wiped the spew right off his desk and looked up at whom was speaking. _Lucas _thought Oliver as he saw his friend shaking him awake where he had obviously dozed off in geography class.

" Dude, you better have a good reason for waking me up. Alba was just about to remove her bra.

"Hey I thought we agreed that Alba was mine. Simpson J is yours,"

"Na ah Alba is mine. And so is Christian Bale."

"Tell me again why you want Christian Bale….Err… never mind"

" What I miss during Geography?"

"Somethin bout the Earth. You think after two semesters we would understand what the topic is finally about.."

"Yeah. Man I can't wait to ..yo wat's up Rico"

Rico the midget of the class just walked in. And he had a big smile. That meant only two things for Rico thought Oliver. He just had a really good day or he had a really good day and then went to jack off. I always wonder how long his….

"Oliver, keep your balls in your head, not on mine."

"What? And why are you so happy.."

" Guess who Samantha Brown just asked to the dance with?" asked Rico

"Fuck off!!!! YOU???" cried both Oliver and Lucas in unison.

"Heck no. She going with James Curtis. I'm going with Renee Watson"

"Then why…Oh never mind….Man" cried Oliver as he packed his things and sat on his chair mumbling to himself. Both Rico and Lucas looked at each other before grinning to themselves.

"Hey Big Daddy Oken, whom you taking to the dance?" asked Lucas.

"I was thinking of Samantha…"

"Come on, you Big Daddy Oken. You the man whom leaves ladies heartbroken is going to go to the dance with his own penis. Ah well I thought better.."

"What Rico? What the fuck you tryin to say..?

"'I'm sayin that you're a dork man. Plain and Lame."

"Whoa, he got you there dude."

"What, Lucas? What you tryin to say now?"

"Listen to Lucas. He knows as well as I do that you're a dork. Who's the last girl that you've been with? Becca the bitch. And she's a slut so that makes it worse. Now look at Lucas here. He got Hannah Montana to flirt with him as well as made out with two babes in school at the same time one of them being of course Lilly your pal. I here have got Miley to kiss me as well as made out with Potter twins"

"Hey, I thought they were faternal.."

"REGARDLESS, you on the other hand haven't so much as kiss a girl making your reputation after graduation to be Most Likely To Trade His Penis For A Vagina all the more likely."

"So you boys are saying I'm haven't been in the game?"

"Dude put it this way. You don't want to be the guy that has to wipe cobwebs from his dick every few years." Said Lucas

Oliver sighed. They are absolutely right. Why haven't I asked or gone out with anyone? Do I like girls? Am I gay? Did Charlie die at the end of Lost? Am I talking out loud?

"Yes!!" said Rico and Lucas together.

"Ok fine tell you what by the end of the school dance which is as we know it one month time, I Oliver Oken solemnly swear that I would make out with a girl"

'Whoa whoa, back up. You can't swear that. The girl could be a cheap slut for all we know"

"Yeah, the girl has to be chaste"

"Nice but hard to get"

"Virgin BUT Hot.With a hot body."

"Not bad in the boob department"

"Someone whom has a boyfriend."

"Wait, WHAT? Come on Rico there is no way I can.." but Rico cut him off

"Look, you want to go from faggert to hot stuff? Then its going to take one hell of a jump to get there so just let it be. Besides if she dumps her man for you, that's her problem not yours."

"In fact, I thinking only one girl." Said Lucas as he looked at Rico, smiling.

"Yeah who else. Miley Cyrus"

"Yeah Miley. She's hot sweet virgin and has a boyfriend by the name of Jake Gay Ryan. Game on I say.."

"Yeah, somemore she's your best friend. Look I know what you're thinking and we probably can't allow this.." said Rico

"Thank you." Cried Oliver ash e buried his head in his hands in relief

"Coz its too easy. No no not kiss Miley Cyrus. Do Miley Cyrus. Pretend she's Jamie Spears."

"WHAT!!!"

"But not like Jamie totally. I mean surely you don't want her pregnant." Said Lucas

"NO NO NO No nononononononononononono…. Miley no way.."

"Yeah I always thought he was a fag. Too bad I was going to make a bet with you" said Rico.

"Wait, wait…what kind of bet?"

"Oh well if you were to succeed I was going to let you have my hot dog shop at the beach. All yours"

"And if I Lose…." Asked Oliver

"Then you are going to have to suck the principal's stick. What say you?"

_What indeed_ thought Oliver in his head. Either way I get to have a hot dog. Come on Oken be frank with yourself. Ha ha frank. _I don't get it._ Frank hotdog get the link? _Huh?_

Never mind._ So, Miley_? I don't know. I always thought Miley as a friend. _HOT Friend._ Okay hot friend but still I don't want to hurt Miley. _Other than down there you mean. _ Yes..I mean NOOO. _Come on we got to focus on what's important. I mean what's so bad. You get to lay Miley. Miley gets laid. Rico gives you his hotdog stand. Jake gets to get out of a relationship so that he can have sex with boys preferably Rico. You and Miley will be perfect. Who's going to get hurt? Have you forgotten the song? If we were a movie. _You'll be the right guy_ And I be the best friend_ You fall in love with..

"OLIVER!!!" cried Rico and Lucas

"So are you game…"

"Okay Ricola…I Oliver Oken swears to la Miley Cyrus by the night of the school dance in 30 days. If not, I would have to suck the penis of Principal Ralph Jones which is rumored to be shorter my thumb. Amen"

"Okay Oken, Lucas. See you later. Don't forget the bet." Cried Rico as he left laughing.

"So Oliver how you going to get her? Any plans…"

"Yes in fact I am cooking up a plan right this instant.…" Oliver proceeded outside the class and into the hallway where Miley was giggling with Lilly and Jake. Lucas simply shrugs his shoulders and lay back near his locker to watch the action unfold.


	2. Chapter 2

**Chapter 2**

Inside Oliver's mind 

Oliver walked up to Miley. OK, what should I say first? Miley You're hot and I wanna lay you on the night of the school dance.

_Are you tryin to be dumb or are you really dumb?_

Who said that?

_It's me…_

Mom?

_No idiot, your common sense. Your helper_

Who?

_Okay never mind just call me Al._

Hi Al! Wait, why the fuck am I dumb?

_Cos you are. Look you wanna get a girl in bed you can't just tell her. Look you have to be smart. Plan it carefully_

Okay, I get it. Wait I don't get it.

_Look , she has a boyfriend right. No relationship on this Earth ever has been perfect. There are bound to be some cracks right. Exploit them_

Oh like how Jake is gay

_No he's not. That's you wanting him to be gay. We won't know for sure until we have more info._

But he's gay. Tommy said all guys with 7 inch dicks are gay and trust me, last time in the boys shower I checked

_What's the MATTER with you?_

What? Are you trying to say I'm jealous. Well I let you kn..

_I DON'T CARE. Look focus on this. Trust me she tell you anything. Besides, she is your best friend._

That's wrong and you know it.

_Who the Fuck are you?_

Yeah. Why the fuck are all these voices in my head?

I'm Bale. Your conscious.

What is that?

Basically I'm the opposite of Al. I tell you what you should do. You should end this bet with that small twerp. It could, no would ruin your friendship with Miley.

But hot dog stand..

Let it go.

Principal's balls

Well, how could you agree to such a thing? Are you tryin to be dumb or are you just dumb?

HEY

Besides what would Lilly think?

_That's a wonderful idea! Good job Bale. Tell Lilly you love Miley._

Why? WHY?

_Cos you and Lilly can plot to get you into Miley's arms. But don't say anything about the sex part. That can wait later._

Why again would she help him?

_Cos Lilly hates Jake and besides she would adore the two of you together. I mean her and Jackson. You and Miley. You guys make such a cute quartet._

I see what you're getting at..

_No Oliver No Foursome. Just use Lilly to get to Miley._

Ok.

Are you mad? Do you wanna ruin your friendship all over a stupid hotdog?

_Look this won't be easy. But like I said. Your reputation and your dignity are stake here. You got two options. Either you lose your virginity to a hot girl, get a hot dog stand as well as maybe fall in love with your best friend or.._

Or?

_Or you can suck principal balls, have your friends be happy with other men and Let Rico gloat over this till you die._

I don't know. Seems like a tough choice..

_Say what?_

Bale what do you think?

Is Jake dick really that long?

Bale!!

Alright alright, look when Al puts it like that is sounds simple but believe me its not. I know that you will most likely to what's right. 

end 

"Lilly!"

"Hey, Oliver." Said Lilly as she checked out her hair in the locker mirror. Lilly and Jackson have been dating for about two months and every night after she talks to Jackson, she would call Oliver telling him how its been going and some advice about boys. After all, Oliver is Lilly longest friend since childhood.

"Lilly, I need to ask you a favour."

"What up my brother? What can the Lillinator do for you? Wait, wait is this about Lucas? Can you can tell him to shove it if he wants to ask me to the dance? I still can't believe that you two are friends!"

"Hey, I need him for my guy needs. There are something we guys just can't share with you girls."

"Like what?"

"Have you noticed that Sharon has the best rack in the school? Or how I wish Josephine would just spread.."

"OK. OK. I get the point. What do you want to ask me?"

"Errr…. Lilly how do you really impress a girl?"

"Say what? Is mr I Leave the Ladies Heartbroken asking me for advice on girls?"

"Well, yes."

"Okay. Okay But first you got to tell me something."

"What?"

"Whose the unfortunate girl whom you have eyes on?"

"I can't tell you that its secret,"

"Cmon Oliver just a clue. Please"

"Nooooo!!!!"

"Just a hint?"

"Ok fine…Ah… She's…er…a…..nice girl.."

"What the fuck of a hint is that?"

"Well, that was your hint. You getting no more from me. My lips are sealed"

" Come on!"

Sighing, Oliver simply scanned the floor till he saw what he was looking for. There were many teachers and students in the hallway all chattering and laughing to each other. Finally he found Miley who was with Jake at the end of the hallway, laughing and flirting with each other.

" Look there. The girl of my dreams"

"MRS SARAH!!!! SAGGY BOOB SARAH?!"

"What?! Are you mental. She's a fourty seven year old woman."

"Is it Michelle?"

"No!"

"Well, only Jake and Miley are left and….Oh no… You got to be kidding?"

"I'm afraid not"

"But you said it was a girl."

"Yes and m…WHAT?!"

"Are you gay? Is that why you like Jake?!"

"No!"

"Is it because of his dick size. I mean I heard the rumors but…"

"NO!!! I mean Miley"

"Oh. …No way!"

"Why not?!" 

"Cos she's my pal. And she loves Jake. And she's happy" 

"But what about me? Look I know its stupid but I got to try. I mean I thought about it a lot.in geography class and I have decided that I love Miley. I cannot deny it."

"But Oliver…"

"Please Lilly. I mean Jake seems nice and all but what if he turns out to be another Lucas? I will always love Miley and never cheat on her. Please Lilly, I care about her a lot. Besides you don't like Jake that much. Will it be so bad if I tried?"

"Well, probably not. Ok, Oliver. I help you get Miley,"

"Thanks, Lilly. You're the best!" And with that he gave her a hug. Lilly simply laughed and hugged him bac. A sort of wild sensational tingle crawl through her skin. She simply brushed it off…. I mean what could it possibly be.

Far off in a classroom on the opposite side of the school, Rico and Lucas were talking in hushed voices. Jackson happened to be walking by heard the two voices. He stopped when he heard Oliver's name. A gut feeling told him to stay quiet and just eavesdrop. Curious he bent down to listen through the door.

"Look dude, I don't know…I mean Oliver's my friend"

"So what? Relax we both want Miley and Lilly right? To be our girlfriends. Oliver's the key. The donut doesn't even realize how lucky he is. Pals to two of the hottest girls in school. And he calls himself Big Daddy?"

"But, Oliver my friend. I mean I kind of hurt his relationship with his girls by hanging out with him. You know what I did. She obviously won't let me forget it.

Jackson removed his head. What in the blue hell were this two idiots planning? He stooped to listen again.

"…and thats when I kissed…well you know…but Oliver been a real pal. Still sticks with us"

"Yeah but none the less we cannot stop what we're doing. I mean we planned this a long time ago"

"Okay fine but let's agree on one thing. You get Miley and I get Lilly like it was made.."

Jackson removed his head. He felt a surge of anger coursed through his veins. How dare they steal his girl. I going to teach them…no wait…on second thought I'm going to let this got through. Oliver seems to be the man in the middle eh?...Better get the whole story before barging in…

Jackson proceeded to leave the hallway in search of Lilly. Rico and Lucas both leave the room almost instantly trying to look innocent before going in separate directions. Both had only two things on their minds..

_Oliver _

_And how long is Jake's dick?_


	3. Chapter 3

**Chapter 3**

**A/N- This is the last chapter in which the fic has a T rating. Will go up to M in next chapter update**.

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"So, Jake what we going to do tonight? Movie?" asked Miley as she and Jake held hands as they walked out of the school gate. Unknowingly to the couple, two figures were emerging from the dustbins near the school gate.

"Oliver you donut where are you?"

"In here!"

"OLIVER! I say at the dustbins not IN IT"

"Well,You could have been more specific!!! And well I…HEY HEY…Someone left Tuna Sandwich in here….Yum"

"Oliver get out of there!" said Lilly as she pulled out Oliver out who was clutching to his tuna sandwich for dear life.

"Hey Hey!! Easy on the threads"

"Look can you just focus!"

"I am focused"

"Ok , well give me that! Look we have to catch up with Miley"

"Tell me again why we spying on her?"

"Cos We need to know what exactly does she and Jake have in common."

"So why can't we just ask her?"

"Look do you want to do it the Easy way or the Lilly way?"

"Well I got to admit … This is more fun"

"Yeah. Look she disappearing..Come on let's catch up,"

"Hey Wait! Wait! Look what someone wrote on the bin. It says that Jake has a sOWWWW!!! Ok Ok! Stop trying to pull my arm off!"

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Elsewhere in a classroom , Cooper and Jackson were talking. Cooper was laughing as Jackson telling him about Rico and Lucas.

"Haaahaaa…You saying that little midget wants Miley back? Hasn't he learned by now?"

"Or maybe he wants Lilly. I mean I didn't hear it too well. A little muzzled.."

"You just saying that cos you're acting like a jealous boyfriend. First you say Lucas then now Rico who's next..OLIVER?!"

"Yeah..No…They're just friends"

"Uhh Jackson I think you better look at this"

Jackson looked out of the window to see both Lilly and Oliver running out of school, with Lilly pulling Oliver's hand

"That son of a bitch!" cried Jackson before storming out of the room.

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"Lilly! Could you scoot over? I think ants are coming up my pants"

"Shhhhh"

"Man they eating my underwear"

"SHHHHH"

Lilly and Oliver were hiding behind some bushes and a small tree in the park where Miley and Jake were talking and joking near the bench.

"And that's why he said Ketchup"

"Ha Ha Jake that was funny…"

"I am, aren't I"

"Ohhh…Stop being so full of yourself"

"I rather be full of you" said Jake as he leans in for a kiss

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"Ewww!!!" cried Lilly and Oliver in unison

"I don't get it Lilly. That was without a doubt one of the lamest jokes I have ever heard. Why the heck is she laughing and smiling?"

"Because donut, she's laughing cos he's cute not cos he's funny"

"I see… Well that means Miley thinks I'm hot!!! I mean she always laugh at my jokes!!"

"No she laughs cos you're funny!"

"But you just said .."

"Look you donut, she's doesn't care about the joke. She cares about him. So that's why she laughs. You know…"

"Ohhh!"

"Now be quiet!" 

"So you're saying girls laugh at me cos I'm funny and not cute. Geee…"

"No Oliver…You are cute and funny"

"You think I'm cute?! Sorry Lilly I'm kinda taken. Dunno how Jackson will react though"

"Oh stop flattering yourself! You do have that nostril problem"

"Who cares…Lilly thinks I'm cute" teased Oliver

"No!"

"Yes!"

"No!"

"Yes!"

"No!"

"No?"

"Yes!"

"So you do think I'm cute…Well well.."

"WHAT?! NO!...Ughh Just concentrate"

"For the record I think you're very cute too"

Lilly just shook her head as she looked at Oliver. _Why was her skin feeling that sensation again?_

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"Look Miley honey, I can't go shopping for new clothes with you today. Marcel wants may to redo this scene in my movie Zombie Slayer Turns Zombie."

"Which scene is that?"

"The one where I get turn into a zombie. I swear I never saw that one coming"

"Righttttt….So anyways I really wanted you to come.There's like this not new skirt that I wanted to buy and I need someone's view on it."

"Why don't you ask Lilly?"

"She's got a date with Jackson."

"Look I really am sorry but I gotta go!"

"But but I rescheduled My Hannah Montana Interview for you. Why can't you do this for me?"

"Look its just shopping. Surely is not that big a deal."

"Yes it is. Well, not the shopping. But I need to know that I can count on you"

"And you can. Right after my scene. Look baby, I'm really sorry but I gotta run. I CALL YOU TONIGHT!!!" shouted Jake as he ran to the limo parked at the roadside. Miley just sighed and walked off.

"Okay Oliver are you thinking what I'm thinking?"

"Yeah….Jake gets turn into a zombie..Never saw that one coming!!"

"Are all guys dumb?"

"On behalf of my gender HEY!"

"Oliver. Miley is troubled that no one wants to go shopping with her. All she needs is someone to follow her. Someone who can help her out and listen to her problems. Someone who will be there for her."

"Are you referring to me?"

"Are you dumb?"

"Yes!"

"Yes it is."

"Ok….HEY!"

"Look go with Miley and be there for her. Now you have to take things slow.She's still in a relationship. You got to let HER fall for you. So just go with her and be there for her. And also one more thing. Don't let her know that you were here so just go to her asked her what's the problem and then go shopping with her. Don't say I told you to!"

"Ok. Will do"

"And Oliver?"

"Yeah?"

"Good luck!"

"Thanks!"

"See you later and CALL ME AT NIGHT ABOUT EVERYTHING!!"

"OK!!! BYE!!!"

Oliver ran off in the direction of Miley. Lilly just sighed as she walked down the path back home, with a happy skip to her steps. _He thinks I'm cute_

"LILLY!"

"Jackson! Hi honey!"

"Don't you hi me! Where is that asshole?"

"Who?!"

"OLIVER. I SAW YOU AND HIM HOLDING HANDS"

"What! Oh no you misunderstood. Look let me explain"

1 second later

"I need more time to explain"

47.65 seconds later

"Could you explain again?"

Another 47.65 seconds later

"Ohhhh! So he wants Miley"

"Yes and he's tryng to go be with her"

"Wow…look Lilly…I'm sorry I'm not a very good boyfriend"

"Its okay. Kiss?"

"Its like you read my mind"

_Should I tell her about Rico and Lucas. No no she might freak out. Better keep this under wraps. I got to find Lucas_.

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" Hey Miley wait up!"

"Hey Oliver!"

"Miley…Hey what's wrong?"

"Huh..Oh its nothing!"

"Come on you always tell me everything. What can Big Daddy Oken do for you?" 

"Well no Jake just blow me over shopping for a scene in a movie. Why can't he just let it go once just once..for me?"

"Well it is a movie and it is his job."

" I know."

"Tell you what I go shopping with you"

"Thanks Oliver but no. I know how you feel about shopping"

"It's okay. Anything for my best pal"

"You're sweet Oliver. Let's go!"

"Yeah I need underwear anyways"

"Ok that part you go solo!"

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Lucas and Rico saw Miley and Oliver making a dash to the mall.

"Looks like its working but I still don't like this" 

"What you getting cold feet? You want your girl or not?"

"Ok fine. Look I gotta go. I got to meet Jackson."

"You do that."

"Ok see you"

_Better keep an eye on him. Got to think of number one_

_Me_


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